NZ577273A - imidazo[1,2-a]pyridine-3-yl-5-substituted pyrimidin-2-yl amines AS PLK1 INHIBITORS - Google Patents

imidazo[1,2-a]pyridine-3-yl-5-substituted pyrimidin-2-yl amines AS PLK1 INHIBITORS

Info

Publication number: NZ577273A
Authority: NZ; New Zealand
Prior art keywords: group; compound; substituted; amino; ethyl
Prior art date: 2006-12-28

Application number

NZ577273A

Other languages

English (en)

Inventor

Takashi Hashihayata

Mikako Kawamura

Morihiro Mitsuya

Yoshiyuki Satoh

Original Assignee

Banyu Pharma Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-12-28

Filing date

2007-12-20

Publication date

2011-03-31

2007-12-20 Application filed by Banyu Pharma Co Ltd filed Critical Banyu Pharma Co Ltd

2011-03-31 Publication of NZ577273A publication Critical patent/NZ577273A/en

Links

-1 imidazo[1,2-a]pyridine-3-yl-5-substituted pyrimidin-2-yl amines Chemical class 0.000 title claims abstract description 66
239000003112 inhibitor Substances 0.000 title claims description 12
102100031463 Serine/threonine-protein kinase PLK1 Human genes 0.000 title description 2
108010056274 polo-like kinase 1 Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 545
150000003839 salts Chemical class 0.000 claims abstract description 39
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 118
238000000034 method Methods 0.000 claims description 118
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 104
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 103
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 91
125000001424 substituent group Chemical group 0.000 claims description 79
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
229910052799 carbon Inorganic materials 0.000 claims description 66
AHRQYOSAXZQCIG-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=C=NC=N[CH]1 AHRQYOSAXZQCIG-UHFFFAOYSA-N 0.000 claims description 62
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
239000002246 antineoplastic agent Substances 0.000 claims description 58
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
230000002401 inhibitory effect Effects 0.000 claims description 37
238000003786 synthesis reaction Methods 0.000 claims description 36
150000002148 esters Chemical class 0.000 claims description 34
230000015572 biosynthetic process Effects 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000000753 cycloalkyl group Chemical group 0.000 claims description 28
125000003386 piperidinyl group Chemical group 0.000 claims description 28
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 27
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 26
125000002393 azetidinyl group Chemical group 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 22
125000000623 heterocyclic group Chemical group 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 19
125000001931 aliphatic group Chemical group 0.000 claims description 18
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
239000003085 diluting agent Substances 0.000 claims description 17
125000001153 fluoro group Chemical group F* 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
239000003937 drug carrier Substances 0.000 claims description 12
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
230000004663 cell proliferation Effects 0.000 claims description 9
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 7
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
229910003827 NRaRb Inorganic materials 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052701 rubidium Inorganic materials 0.000 claims description 3
XVSOLNIURSFPEU-UHFFFAOYSA-N benzyl 4-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate Chemical compound C1CC(C(=O)N(C)OC)CCN1C(=O)OCC1=CC=CC=C1 XVSOLNIURSFPEU-UHFFFAOYSA-N 0.000 claims description 2
SGHLIDFIGPEARR-IBGZPJMESA-N benzyl 4-[4-[(1s)-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]benzoyl]piperidine-1-carboxylate Chemical compound C1=CC([C@@H](NC(=O)OC(C)(C)C)C)=CC=C1C(=O)C1CCN(C(=O)OCC=2C=CC=CC=2)CC1 SGHLIDFIGPEARR-IBGZPJMESA-N 0.000 claims 3
GNFLFHZJXXFDRA-UHFFFAOYSA-N 1,2-dimethylpyrrole Chemical compound CC1=CC=CN1C GNFLFHZJXXFDRA-UHFFFAOYSA-N 0.000 claims 1
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 112
238000006243 chemical reaction Methods 0.000 description 111
239000000047 product Substances 0.000 description 102
239000000243 solution Substances 0.000 description 102
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
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238000005160 1H NMR spectroscopy Methods 0.000 description 37
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
239000012044 organic layer Substances 0.000 description 35
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 34
206010028980 Neoplasm Diseases 0.000 description 32
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102000014150 Interferons Human genes 0.000 description 30
108010050904 Interferons Proteins 0.000 description 30
239000003480 eluent Substances 0.000 description 30
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
229920006395 saturated elastomer Polymers 0.000 description 23
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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238000010898 silica gel chromatography Methods 0.000 description 21
201000011510 cancer Diseases 0.000 description 20
239000012046 mixed solvent Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 18
235000017557 sodium bicarbonate Nutrition 0.000 description 18
229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
230000000694 effects Effects 0.000 description 17
229910052697 platinum Inorganic materials 0.000 description 17
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239000000126 substance Substances 0.000 description 17
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
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PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 15
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101100464293 Caenorhabditis elegans plk-1 gene Proteins 0.000 description 12
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238000010899 nucleation Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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230000000865 phosphorylative effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
150000003058 platinum compounds Chemical class 0.000 description 1
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239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
DERJYEZSLHIUKF-UHFFFAOYSA-N procarbazine hydrochloride Chemical compound Cl.CNNCC1=CC=C(C(=O)NC(C)C)C=C1 DERJYEZSLHIUKF-UHFFFAOYSA-N 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
229940087463 proleukin Drugs 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000006628 propoxycarbonylamino group Chemical group 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
229940099538 rapamune Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000022983 regulation of cell cycle Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000005834 sharpless asymmetric dihydroxylation reaction Methods 0.000 description 1
229950001403 sizofiran Drugs 0.000 description 1
239000004055 small Interfering RNA Substances 0.000 description 1
208000000587 small cell lung carcinoma Diseases 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019795 sodium metasilicate Nutrition 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
VIDRYROWYFWGSY-UHFFFAOYSA-N sotalol hydrochloride Chemical compound Cl.CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 VIDRYROWYFWGSY-UHFFFAOYSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
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239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940120982 tarceva Drugs 0.000 description 1
230000008685 targeting Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229940063683 taxotere Drugs 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 1
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
229960000902 thyrotropin alfa Drugs 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
229940086984 trisenox Drugs 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
229940054937 valstar Drugs 0.000 description 1
229940099039 velcade Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
239000013603 viral vector Substances 0.000 description 1
230000005727 virus proliferation Effects 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000012610 weak anion exchange resin Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940053867 xeloda Drugs 0.000 description 1
238000012447 xenograft mouse model Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
229940033942 zoladex Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NZ577273A 2006-12-28 2007-12-20 imidazo[1,2-a]pyridine-3-yl-5-substituted pyrimidin-2-yl amines AS PLK1 INHIBITORS NZ577273A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2006356575		2006-12-28
JP2007265783		2007-10-11
PCT/JP2007/075224 WO2008081910A1 (en)	2006-12-28	2007-12-20	Novel aminopyrimidine derivatives as plk1 inhibitors

Publications (1)

Publication Number	Publication Date
NZ577273A true NZ577273A (en)	2011-03-31

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Country Status (24)

Country	Link
US (1)	US7977336B2 (de)
EP (2)	EP2116543A4 (de)
JP (1)	JPWO2008081914A1 (de)
KR (1)	KR101481388B1 (de)
CN (1)	CN101573361B (de)
AR (1)	AR064619A1 (de)
AU (1)	AU2007340530B2 (de)
BR (1)	BRPI0718966B8 (de)
CA (1)	CA2668738A1 (de)
CL (1)	CL2007003758A1 (de)
CO (1)	CO6190523A2 (de)
CR (1)	CR10784A (de)
EC (1)	ECSP099324A (de)
GT (1)	GT200900124A (de)
IL (1)	IL198675A0 (de)
MA (1)	MA31109B1 (de)
MX (1)	MX2009004920A (de)
NO (1)	NO20092770L (de)
NZ (1)	NZ577273A (de)
PE (1)	PE20081845A1 (de)
RU (1)	RU2458062C2 (de)
SV (1)	SV2009003258A (de)
TW (1)	TW200835485A (de)
WO (2)	WO2008081914A1 (de)

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JP6559228B2 (ja)	2014-09-17	2019-08-14	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	肥満症及び糖尿病の治療に有用なテトラヒドロイソキノリン誘導体及び医薬組成物
WO2018191171A1 (en) *	2017-04-10	2018-10-18	City Of Hope	P38 gamma inhibitors and method of use thereof
US12398132B2 (en) *	2019-07-10	2025-08-26	Aucentra Therapeutics Pty Ltd	Derivatives of 4-(imidazo[1,2-a]pyridin-3-yl)-n-(pyridinyl)pyrimidin-2-amine as therapeutic agents
BR112022001158A2 (pt) *	2019-07-24	2022-05-17	Merck Patent Gmbh	Derivados de 4-(imidazo[1,2-a]piridin-3-il)-pirimidina
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2007
- 2007-12-18 US US12/002,546 patent/US7977336B2/en active Active
- 2007-12-20 CA CA002668738A patent/CA2668738A1/en not_active Abandoned
- 2007-12-20 AU AU2007340530A patent/AU2007340530B2/en active Active
- 2007-12-20 JP JP2008552168A patent/JPWO2008081914A1/ja not_active Ceased
- 2007-12-20 AR ARP070105784A patent/AR064619A1/es not_active Application Discontinuation
- 2007-12-20 TW TW096149071A patent/TW200835485A/zh unknown
- 2007-12-20 EP EP07851126A patent/EP2116543A4/de not_active Withdrawn
- 2007-12-20 NZ NZ577273A patent/NZ577273A/en not_active IP Right Cessation
- 2007-12-20 KR KR1020097013324A patent/KR101481388B1/ko active Active
- 2007-12-20 CN CN2007800488795A patent/CN101573361B/zh active Active
- 2007-12-20 MX MX2009004920A patent/MX2009004920A/es active IP Right Grant
- 2007-12-20 CL CL200703758A patent/CL2007003758A1/es unknown
- 2007-12-20 BR BRPI0718966A patent/BRPI0718966B8/pt active IP Right Grant
- 2007-12-20 WO PCT/JP2007/075240 patent/WO2008081914A1/ja not_active Ceased
- 2007-12-20 RU RU2009128966/04A patent/RU2458062C2/ru active
- 2007-12-20 EP EP07851112A patent/EP2114942B1/de active Active
- 2007-12-20 WO PCT/JP2007/075224 patent/WO2008081910A1/en not_active Ceased
2008
- 2008-01-02 PE PE2008000054A patent/PE20081845A1/es not_active Application Discontinuation
2009
- 2009-05-08 CR CR10784A patent/CR10784A/es not_active Application Discontinuation
- 2009-05-10 IL IL198675A patent/IL198675A0/en unknown
- 2009-05-12 CO CO09048000A patent/CO6190523A2/es not_active Application Discontinuation
- 2009-05-12 GT GT200900124A patent/GT200900124A/es unknown
- 2009-05-12 EC EC2009009324A patent/ECSP099324A/es unknown
- 2009-05-12 SV SV2009003258A patent/SV2009003258A/es active IP Right Grant
- 2009-07-23 MA MA32115A patent/MA31109B1/fr unknown
- 2009-07-27 NO NO20092770A patent/NO20092770L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP2114942A4 (de)	2010-09-08
EP2114942A1 (de)	2009-11-11
NO20092770L (no)	2009-09-25
MA31109B1 (fr)	2010-01-04
SV2009003258A (es)	2010-08-23
ECSP099324A (es)	2009-06-30
CN101573361B (zh)	2012-05-30
WO2008081910A1 (en)	2008-07-10
KR101481388B1 (ko)	2015-01-12
BRPI0718966A2 (pt)	2014-01-07
PE20081845A1 (es)	2008-12-27
AR064619A1 (es)	2009-04-15
BRPI0718966B8 (pt)	2021-05-25
EP2116543A4 (de)	2010-09-08
GT200900124A (es)	2010-11-03
CA2668738A1 (en)	2008-07-10
AU2007340530A1 (en)	2008-07-10
AU2007340530B2 (en)	2012-09-13
KR20090092822A (ko)	2009-09-01
BRPI0718966B1 (pt)	2020-11-17
CR10784A (es)	2009-09-16
EP2116543A1 (de)	2009-11-11
CN101573361A (zh)	2009-11-04
RU2458062C2 (ru)	2012-08-10
MX2009004920A (es)	2009-05-21
CL2007003758A1 (es)	2008-07-04
EP2114942B1 (de)	2012-10-31
IL198675A0 (en)	2010-02-17
US7977336B2 (en)	2011-07-12
TW200835485A (en)	2008-09-01
US20080305081A1 (en)	2008-12-11
CO6190523A2 (es)	2010-08-19
JPWO2008081914A1 (ja)	2010-04-30
WO2008081914A1 (ja)	2008-07-10
RU2009128966A (ru)	2011-02-10

Legal Events

Date	Code	Title	Description
2011-04-29	ASS	Change of ownership	Owner name: MSD K.K., JP Free format text: OLD OWNER(S): BANYU PHARMACEUTICAL CO., LTD.
2011-07-29	PSEA	Patent sealed
2012-01-27	RENW	Renewal (renewal fees accepted)
2015-06-26	LAPS	Patent lapsed

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